5-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester → 5-(3-Methanesulfonylamino-propyl)-thiophene-2-carboxylic Acid Methyl Ester

HRID 1699000Notes

Reaction equation

HRID 1699000 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][CH:9]=1)=[O:4]>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 1

HCID 537526885-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 536710815-(3-Methanesulfonylamino-propyl)-thiophene-2-carboxylic Acid Methyl EsterYield 97.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(3-methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester (3.0 g, 10.9 mmol) in EtOAc (100 mL) and MeOH (50 mL) was hydrogenated with 10% Pd/C (680 mg) at 50 psi for 7 h. The solution was filtered through a pad of Celite with the aid of MeOH and was concentrated in vacuo to provide the title compound as an off-white solid (2.95 g). 1H NMR (300 MHz, CDCl3) δ7.62 (d, 1H), 7.23 (d, 1H), 4.29 (m, 1H), 3.85 (s, 3H), 3.18 (q, 2H), 2.93 (m, 5H), 1.96 (m, 2H).

Workup

  1. filtrationThe solution was filtered through a pad of Celite with the aid of MeOH
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-9c2907ba3f3e4feab63d47f6413524eb
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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